$179 Find Cheap Flights from Hawaii to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Hawaii to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hawaii to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hawaii to Chicago

Mon, Aug 17 - Fri, Oct 30
Delta Logo
9:55 pm - 5:00 pm
LIH
-
ORD
14h 05m
1 stop
Delta Logo
12:50 pm - 7:14 pm
ORD
-
LIH
11h 24m
1 stop
$424Delta
Fri, Oct 30 - Sat, Nov 7
Multiple Airlines Logo
7:21 pm - 6:53 pm
LIH
-
ORD
18h 32m
2 stops
Multiple Airlines Logo
2:25 pm - 1:47 pm
ORD
-
LIH
27h 22m
1 stop
$429Multiple Airlines
Wed, Sep 23 - Wed, Sep 30
Delta Logo
9:54 pm - 6:01 pm
LIH
-
ORD
15h 07m
1 stop
Delta Logo
6:00 am - 5:40 pm
ORD
-
LIH
16h 40m
2 stops
$430Delta
Thu, Aug 20 - Wed, Aug 26
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
Alaska Airlines Logo
6:01 am - 2:48 pm
ORD
-
KOA
13h 47m
1 stop
$434Alaska Airlines
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$434Southwest
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
3:15 pm - 11:35 am
HNL
-
MDW
16h 20m
1 stop
Southwest Logo
7:30 am - 9:10 pm
MDW
-
HNL
17h 40m
2 stops
$440Southwest
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
1:25 pm - 5:59 am
LIH
-
ORD
11h 34m
1 stop
American Airlines Logo
9:10 pm - 11:48 am
ORD
-
LIH
19h 38m
1 stop
$482American Airlines
Tue, Oct 13 - Sat, Oct 24
Alaska Airlines Logo
10:36 am - 1:25 pm
KOA
-
ORD
21h 49m
1 stop
Alaska Airlines Logo
2:21 pm - 2:48 pm
ORD
-
KOA
29h 27m
1 stop
$494Alaska Airlines
Mon, Aug 17 - Mon, Aug 31
American Airlines Logo
9:45 pm - 2:22 pm
KOA
-
ORD
11h 37m
1 stop
American Airlines Logo
6:59 am - 1:58 pm
ORD
-
KOA
11h 59m
1 stop
$564American Airlines
Tue, Nov 3 - Wed, Nov 4
United Airlines Logo
11:11 am - 5:01 am
ITO
-
ORD
13h 50m
1 stop
United Airlines Logo
2:00 pm - 7:04 am
ORD
-
ITO
21h 04m
2 stops
$807United Airlines
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Good to know

Low season

January

Cheapest flight

$179
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Kahului to Chicago O'Hare Airport

FAQs for booking flights from Hawaii to Chicago

  • How does KAYAK find such low prices on flights from Hawaii to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $5,975
Business Class flights to Chicagofrom $3,805
Premium Economy Class flights to Chicagofrom $2,005
Economy Class flights to Chicagofrom $334